


Starting Over Is Hard To Do

by Codependent_Idiots



Category: Supernatural
Genre: AU, First Kiss, Guardian Angels, M/M, Meet-Cute, Mutual Attraction, Soulmates, Wincest - Freeform, Wincest AU - Freeform, love? at first sight, only related in chapter one
Language: English
Status: In-Progress
Published: 2019-07-17
Updated: 2020-04-13
Packaged: 2020-06-30 03:41:31
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 7,879
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19844833
Author URL: https://archiveofourown.org/users/Codependent_Idiots/pseuds/Codependent_Idiots
Summary: The Winchesters Are Dead.But what else is new?Given an option, will Sam and Dean take a chance at something they were never allowed to have before?





	1. Dead & Buried

**Author's Note:**

> Hi! This is my first story for the SPN fandom, and let me say, I am anxious. I hope it's good and lives up to the other amazing writers who post here.
> 
> (let me warn ya'll, I am terrible at editing, so sorry in advance)
> 
> Find me on tumblr under 'codependent-idiots' - all wincest/supernatural stuff :)
> 
> This is just the first chapter, so it's a lil short! Enjoy!

"Never thought I would see this day," the man in front of Dean said, smiling sadly at him. The man was in a fine suit, hair impeccably brushed, teeth blindingly white.

He was an Angel. 

Dean glanced around him - an all white room, empty except for the two chairs, one which he occupied, the other by the Angel. He had chains around his wrists and ankles, binding him.

"It is just a precaution, you know. It is no secret how aggressive you can be, Dean Winchester.” Dean didn’t respond, not rising to the bait. “We have been waiting a long time for you to come here. You  _ do _ know where you are, don’t you Dean?”

“Where’s Sam?”

“Oh, he speaks,” the Angel said with that same small smile. “And yet, instead of concerned for himself, he thinks of the one he cares for most.” Dean felt an ugly flush creep up his neck to his face, but he steeled his face into his best ‘i-will-fucking-kill-you’ look. The Angel let out a small chuckle. “Samuel is close, but not here yet. Any minute now, he will be though. Have you figured it out yet?”

Dean felt his heart pounding in his chest, his blood rushing in his ears. But was it really though?

“I’m dead.” The Angel just had that sad smile again as he nodded. “For good?” Another nod. “How’d it happen this time?”

“Shot in the heart when someone tried to steal your car. Could not be saved. Brave Sam did try, of course he did. He ended up with a bullet in the back and in his lungs for you.”

“Shit,” Dean muttered, eyes closing. Sam was going to die, because of him,  _ again _ . Seriously, they couldn’t catch a fucking break, could they? “So who the hell are you? My personal tour guide? Cuz no thanks, I don’t want what you’re selling.”

“Oh, but I think you might,” he said simply, standing up now. “My name is Marco. And you can consider me… a Guardian of sorts.”

Dean snorted. “A Guardian Angel? Didn’t I already have Cas?”

“Castiel was more a pet, was he not?” Dean snorted and gave a small nod. “He is watching, and he is not amused by my statement, even though he knows it's true. He is not arguing. Oh!” Marco snapped his fingers, and Dean watched as the wall across from him lit up, as if for a movie.

It was Sam, bleeding out on a hospital bed, tube down his throat, the machine next to him beeping erratically.

“Sammy!” Dean screamed, knowing that the image couldn’t hear him, but that didn’t stop him.

_ “He’s flatlining! 1-2-3-CLEAR!”  _ Dean heard the buzz, the sizzle of Sam’s skin.  _ “We need to stop the bleeding and get this man’s heart started up again. 1-2-3-CLEAR. He’s not responding!” _ Dean had tried to stop it, but the tears began to slip down his cheeks as he watched Sam grow paler, the blood stain larger.  _ “I’m calling it. Time of death, 10:32PM. _ ” Marco snapped his fingers again, and the image faded.

“Why did you show me that?” Dean muttered, angry now.

“To show you that you are not alone. Not now, not before, and not again.” Dean met his eyes, and now Marco smiled, all white teeth and blinding energy. “Want to hear “what I’m selling” now, Dean Winchester?”

…

“Hello Samuel.”

“It’s Sam,” he muttered before he even opened his eyes, raising his head to look at the woman across from him. “Who the hell are you?” He shifted his arms, feeling the chains binding him in place.

“A friend in your most desperate time of need.”

“No thanks,” he mumbled, head dropping again.

“Hmm, death does not agree with you, does it. You did put up a most remarkable fight.” Sam looked up again, eyes hard. “Do you remember dying?”

“I remember enough. Where’s my brother?” The woman smiled, and he finally got a decent look at her - dress suit, hair in a tight bun, impeccable taste; between her and the all white room, he had a feeling that he could guess who she was. “You’re an Angel?”

“I am. My name is Diana. You are dead. Your brother is dead. The Winchesters are dead. There is no resurrection for you this time.”

“Great. Thanks for the pep talk. So what do you want from me? And where the fuck is Dean?”

“You care for him greatly, do you not? I am sure you are aware, that there is no hiding miniscule details at this point in time, yes?” Sam wore his best bitch-face as he eyed her. She just chuckled. “Dean is fine. He is being made the same offer that you will receive. Even has the Castiel stamp of approval.”

“Yeah right. I’ll pass. Just throw me in some corner for the rest of eternity.”

“Oh no, we would never let such potential go to waste like that. Not with you, Sam Winchester.” Sam just leaned his head back, staring at the white ceiling, not responding. “You will listen, if nothing else. I think you will see that this is something you will want, more than you can imagine.”

…

“You gotta be fucking kidding me,” Dean muttered, staring at Marco, who was seated across from him again.

“I can assure you,I am not. Sam is just on the other side of this wall, hearing the same offer. We extended it to you both. After all, what is one without the other?” 

Dean sat back in his seat, stomach twisting. What they were offering, even  _ suggesting _ , went against everything he had tried so hard to hold on to in his life, never letting his heart take the lead. If he did this, if he let them do this to him and Sam, then there wouldn’t be anything to hold him back. Nothing to hold  _ either _ of them back anymore, leaving them to face these …  _ feelings _ , once and for all.   
  
“What do I gotta do?”

…

Sam looked at Diana, who just smiled.

“You’re crazy.”

“Am I? As if someone with your intelligence does not know what it means for two souls to share a heaven, to share a bond such as yours and your brother’s.” Sam was quiet as he thought about that - yeah, he knew, the echo of Ash’s words all those years ago permanently scarred in his heart. 

It left him facing things he didn’t want to face.

“If it makes you feel any better, Sam, Dean is considering the offer. Because he knows what it means for the two of you.”

Sam let out a shaky breath, nodding his head. He had always known it was there, the thing they never talked about, and now they were being offered an out.

“Okay. If he agrees, then so do I.”

…

Castiel closed his eyes and his face twisted down as he heard the twin screams echo in the air, followed by the woosh of angel wings, and then silence.

It had not been an easy argument, convincing them to give this chance to the Winchesters - the same ones who had destroyed Heaven one too many times, had fought tooth and nail against anything supernatural. But he had won out, and now they had a chance to live their lives.

And he would be watching.

…

  
  



	2. First Meeting

**Summary for the Chapter:**

> Sam and Dean get to meet for the first time, all over again.

**Notes for the Chapter:**

> Fair warning, I am TERRIBLE at editing.

**_Dean Cadwell, 26 years old:_ **

“Cadwell! Get your ass in gear!” Dean jerked, shaking his head. He had been standing by his locker in the back of the garage he worked in, slamming the door shut with a resonating bang. He had been struck by a wave of almost deja-vu, which was fucking weird, but he ignored it and moved out to the front, leaning against the car he was supposed to be working on. Some beat up VW Bug was what was waiting for him.

Fuck, this job was exhausting and his boss was a grade-A asshat, but it was a job, and he was damn good at it - he had always had a gift with cars, and cars always needed to be fixed. Running a hand through his dark blonde hair and letting out a tired sigh, he rolled up his sleeves and got to work.

…

**_Sam Westing, 22 years old:_ **

“Come on Sam, our shift starts in 20 minutes!” Sam turned from where he had been standing in front of the bathroom mirror. He had felt off there for a few minutes, but putting it down as the stress of finals coming up, he shrugged it off and slipped his maroon button down for work over his tshirt.

“Yeah yeah, I”m coming, hold your horses,” he muttered, putting his nametag on as he grabbed his keys and met his roommate, Conner, in the living room. “Let’s go already.” The two of them hurried out of the college apartment, power walking the two blocks to the small cafe they worked at. Sam’s mind was thinking of the weird wave of feelings he had earlier. He shook his head, making his chestnut brown hair shift and curl around his ears. His eyes trail to the garage down the street from the cafe, a strong feeling twisting in his gut. Ignoring it, he heads inside to start his shift.

…

“Okay Cadwell, lunch time!” Dean looked up at his coworker Max. Max was a pain in the ass, but he was better than eating lunch with their fucking boss, so Dean dealt with it. Besides, if Max was coming with him, then that meant his scrawny ass could pay for lunch this time.

“Fine, but you’re buying.” Max nodded, pulling his long hair down from its ponytail. 

“Sounds great. Let’s get eating. I saw a hot blonde walk into that cafe down the street and I wanna go check her out. Waitress uniform man.”

“That’s called stalking, and it will get you fucking arrested,” Dean said, getting up and washing the grease off his hands. Max just scoffed as the two of them made their way down the street. 

“Dude you didn’t see her  _ legs _ . Legs for fucking miles man.” Dean snorted as he and Max went to sit at a small table in the back. Max was swiveling his head around, grinning when their server came up, the leggy blonde woman in tow.

Dean was pretty sure this is what being struck by lightning felt like.

“Holy fuck,” he muttered, raising his green eyes to meet bright, surprised hazel ones. 

He was pretty sure he had just seen the most gorgeous person to ever walk the fucking planet. Dean was no small man, resting just at 6 feet tall, and this guy easily had three inches on him, if not a little more. With his brown hair that curled up by his ears, those fucking eyes, and soft lips, Dean didn’t know if he could look away. He blinked and forced himself to glance down to the silver nametag on his shirt.

_ Sam _ .

…

Sam had watched the two guys come in, his heart tight in his chest as they sat in the back. They had come in a few times before, he knew from their outfits - and their messiness - that they worked at the garage.

He gripped his order book and turned to the girl he was training.

“Okay Hannah, just follow my lead. You’re doing great so far.” The girl beamed at him, batting her eyes affectionately as she laid a small hand on his arm.

“What would I do without you to watch over me Sam?” she asked, giggling as she added a little pressure to her touch. Sam was flattered, of course, but he had had enough of girls to last him for a while, so he moved her hand with a soft smile.

“You would do your job. Come on.” He led the way, and she followed easily enough. This should have been easy - they would get burgers and coffee, he was sure; not like the cafe offered too wide of a selection.

He felt his introduction die in his throat though as he locked eyes with one of the guys. He was handsome, like  _ model _ handsome, with these chiseled cheekbones and these playful green eyes and man the fucking freckles, and Sam was pretty sure those lips should be illegal if just looking at them sent his mind into a tailspin.

He let his eyes fall to the small frayed patch on the front of his coveralls. 

_ Dean. _

…

Sam let out a small cough, clearing his throat before he smiled at the two of them, trying not to focus on how the one with the pretty green eyes -  _ Dean _ , his nametag said - was watching him.

“Hi guys, I’m Sam. This is Hannah, my trainee for today. What can we get you?” Sam felt like he was stumbling over his words, but the guy finally looked away to glance at what they offered. The guy across from him was already speaking, eyes focused completely on Hannah’s chest.

“Cheeseburger and a coffee, black,” he said, not even blinking now as he stared at Hannah, who looked at Sam, obviously uncomfortable. Before Sam could do anything, the man yelped and looked at Dean in anger.

“You’re being a fuckin’ perv. Now stop before your dumbass gets us kicked out. Sorry,” he said, looking at Sam and Hannah. “He’s an asshole, but he’s harmless. I’ll have a double cheeseburger with extra onions, coffee too.” Sam nodded and wrote down their orders and hurried away, pushing Hannah in front of him. Dean watched him go, eyes on his ass briefly before he looked at Max, who was glaring at him.

“Man you had to make me look like a freak, I was gonna totally score with her!” Max said, and Dean kicked him again.

“You’re a fucking perv, and she’s gonna call the cops on you and I’ll just sit back and watch your ass get dragged to jail. I told you you were being fucking creepy.”

“Oh and like you weren’t?! I saw you checking out the twink.” Dean felt his eye twitch - some part of his brain that had been dormant kicking into gear at hearing anyone talk about this guy he just met,  _ Sam _ , in any derogatory way. He kicked Max again before he stood up and moved to the counter, where Sam was wiping down some napkin holders.

“Hi.” Sam looked up and gave a small smile, and Dean had to bite his lip to stop the groan - the kid had fucking dimples, and fuck his eyes kept changing colors as he looked at Dean. Sam stared at the hot mechanic, unable to stop the grin when he found those green eyes locked on him. “I wanted to apologize again for my friend. He’s really bad with women, for obvious reasons.” Sam nodded and chuckled a bit.

“It’s okay. Hannah was creeped out, but kind of flattered too, but don’t tell either of them that I said that.” Dean laughed and held his hand out. 

“I’m Dean.” Sam grabbed his hand, giving it a quick shake before he pulled back.

“Sam,” he said, reintroducing himself. Dean grinned and leaned on the counter, lips turning up in a small smirk, tongue darting out to lick his lips - he didn’t miss the way Sam’s eyes flicked to his lips before he looked back into his eyes. 

“It’s nice to meet you, Sam.” Before they could get to talking more, Hannah popped her head out of the kitchen, smiling at Dean and batting her eyes at him - Sam rolled his eyes and turned to his coworker, his face falling into an unimpressed deadpanned look that Dean instantly dubbed ‘bitchface’ in his mind. 

“Oh, I was just about to bring your orders out,” she said, stepping out of the kitchen with a tray of food.

“That’s fine, I can get it,” he said, flashing her a standard flirty smirk as he grabbed the tray from her, watching her face turn pink before he looked back at Sam, face growing softer, smile just barely there as he met cool hazel eyes. “Talk to you later Sam.” Sam nodded, trying to will his face to cool down from the blush he knew was spreading over his face and down his neck as he watched Dean walk back to his table. He felt Hannah nudge him in the arm before she began to giggle, turning to the kitchen.

“Conner you just missed Sam making a fool of himself!” Sam facepalmed and looked at her, seeing her giggle some more.

“Dammit why did I get stuck with kitchen duty today?!” Conner grumbled, stepping out of the kitchen and looking at his roommate. “What did your stupid ass do now?”

“I’m smarter than you,” Sam easily, his eyes betraying him by looking over at Dean, who seemed to be talking animatedly with his friend. Conner followed his eyes and snorted in laughter.

“Dude, you gotta get laid.”

…

Dean let Max go up to the counter to pay for their check, apologizing to Hannah again, who smiled at him as he chatted her up. Dean himself leaned against the wall near the door to the cafe, trying his damndest to not stare at Sam, who was leaning over a table near the back, wiping it down and clearing it off. 

As Max walked back towards him, he saw where Dean was looking and laughed in his face.

“Man, stop staring at his ass and get going. We gotta go back to work before the boss chews us a new one.” Dean nodded, looking away when he saw Sam glance up at them. He briefly looked up, catching those fucking eyes that looked like they held the fucking world in them, and gave Sam a small nod. Sam returned the gesture, pulling his bottom lip between his teeth before he went back to work.

Oh, Dean was screwed.

…

Dean was in the back of the shop, underneath a large battered SUV while some 80s rock played off the speakers on his phone. He had finished up the Bug when they returned from lunch - which was a feat considering he kept thinking of warm hazel eyes - and was now working on this hunk of junk. He was just kind of loss in his head, when his boss - that asshole Lenny - screamed for him.

“CADWELL! GET YOUR ASS OUT HERE TO THE FRONT!” Dean groaned but grabbed his phone and shut off his music as he got back onto his feet. He entered the main work area of the garage and headed out to the back, where a truck was waiting, six beat up mangled messes of cars in its cargo hold. Dean’s eyes flickered to one car in particular - the back end was in pretty decent shape, but the front was twisted and warped and bent essentially into a pretzel, as if it had been wrapped around a tree. Dean was thrown out of his admiration of the car when Lenny shoved his elbow into his side.

“Okay kid,” he said, snorting in between words in a huff, making Dean grimace. “These cars are all salvage and trash. So we’re gonna scour them, get what is still usable, and keep the rest for scraps.”

Dean didn’t like the sound of that, his eyes falling to the twisted black car on the end again. Some type of Chevy, that was all he could tell. 

He wondered if it could be fixed up.

...


	3. My Hero

**Summary for the Chapter:**

> Castiel wants to interfere, so Dean comes to the rescue.

**Notes for the Chapter:**

> FINALLY. SORRY FOR THE DELAY. I WILL TRY TO UPDATE FASTER NEXT TIME I PROMISE.  
> ...

Dean had tried to not make a habit of it, but fuck, he was stuck. He ate lunch at the cafe every day he worked - it was convenient, sure, but also… 

Okay, he wouldn’t say he was “stalking” per se, but every day he got to see Sam made his day just a little bit brighter. And if the same smile Sam gave him every day didn’t mean he wasn’t happy to see Dean, the man would eat his own boot!

And he wasn't wrong. The only thing that seemed to get Sam through the last of his finals and into the summer without absolutely hating his job was the fact that the hot guy from the garage came in practically every day, and made sure to be seated where Sam could help him. 

Every time Dean came in, he always told himself he was going to finally man the fuck up and ask Sam out, but he always chickened out and left before he could make a fool of himself. Which was an excuse and he knew it - Dean was a playboy if there ever was one, and quite a few ladies, and a few unlucky guys, knew this firsthand. He wasn’t one for wooing and romance and relationships.

But fuck, that was all he wanted with this guy, and he barely knew him! 

Sam could say the same - his last major relationship had gone up in flames, and he had tried to just casually date, maybe even a one night stand, but it hadn’t worked for him. But everytime he saw Dean, he just wanted to worship every part of his body and keep him by his side and love him and  _ Sam was a little freaked out, he didn’t even know the guy! _

Every day they saw each other, they made light conversation and shy smiles, but that was all. They both really wanted to ask the other out, but weren’t sure how to approach the subject when all the really knew about the other were their first names and where they worked.

…

  
  


…

Castiel hummed in concerned thought as he watched the two of his friends dance around each other. No, he wouldn’t interfere, but it had been going on a month since Dean had walked into the cafe and had seen Sam, and he had yet to make a move. Castiel didn’t understand, but perhaps they just needed some motivation to talk to each other a little more.

“I believe that is considered interfering, Castiel,” Marco said from his seat next to the dark-haired angel.

“No, not at all. Persuasion at it’s best,” he said in his serious voice, a twitch to his lips hiding his smile. “For them, I am helping, as I always have tried to do.” He twitched his finger a bit, and watched the scene unfold.

…

Hannah had called in, and Connor had bailed early, so Sam was closing up the cafe with the night manager. He stood at the counter, mentally keeping tally of the cash register as he filled out the nightly money report. They weren’t closed, not for another 10 minutes, but anyone rarely came in this late, so he wasn’t concerned that it was just him, a 6 foot 4 almost college senior and a small 5 foot woman for the night. He could easily take someone down - thanks to Connor harassing him to take kick-boxing with him during freshman year, and no one would dare mess with Sherry, she would shank someone in heartbeat - that woman was fucking scary.

So Sam didn’t think of anything when he heard the backdoor to the kitchen swing open, not even bothering to look behind him while he called out, “Hey, get the kitchen count done?”

“No, something came up.” Sam stilled as a rough voice answered him, the cold metal of a gun placed against the back of his neck. “Don’t fucking move.”

…

Dean was finishing up at the garage, locking the front gate, when he decided to stop at the cafe. He thought the blonde, Hannah, would be working, and if he flirted just enough, maybe she would tell him when Sam was working next. Grabbing his tools - like he would use the crappy tools his boss provided - he made his way down the street/

He stopped right at the edge of the front windows, stepping back when he took a quick peek inside.

Sam was at the front counter - which was weird in itself, Sam didn’t usuallly cllose from what Dean could tell - and behind him was a man in a dark jacket and a ski mask over his face, the glint of something silver in his hand.

“Oh hell no,” Dean muttered, setting down his toolbox and grabbing a heavy iron wrench, gripping it in both hands. Moving towards the back of the building, he saw the side door propped open with a cement block. Slipping inside, he tried to step as lightly as his workboots could. He saw the door to the office by the kitchen open, a small woman tied up in a chair, her head limp on her shoulders. “Shit.” He moved closer, pressing two fingers to her neck. Her pulse was beating rapidly. 

Okay, so the guy didn’t kill her. Good. Dean was still going to clock him over the head though.

Moving as slow as he could, he was finally near the door that lead to the front; if he shifted just right,he could see Sam, with a gun pointed at his head.

…

“Listen, you don’t have to do this-”

“Give me the fucking money, and I know there’s the fucking safe too. Unless you wanna end up like your boss. Pretty thing, isn’t she? You’re not too bad to look at either big boy.” Sam grimaced as the gun was pressed deeper into his neck. “Yeah, maybe I’ll get the money, and then bend your pretty little self right over the counter and just-”

The guy let out a suprirsed yelp as something collided with the side of his head, knocking him down. Sam turned around to see Dean standing there, a wrench in his hands.

“You okay Sammy?” Sam flushed but nodded before he looked down at the guy. 

“Did you-”

“Nah, he’s fine. Call the cops. Your boss is knocked out in her office.” Sam nodded and reached for his phone, making the call.

…

Sam and Dean sat outside the cafe as the last cop car pulled away.

“Not how I expected my night to end,” Sam said, shaking his head a bit so he could hide behind his hair. 

“Me neither. Why were you working so late any way? Don’t you usually work the lunch shift?”

“Covering for someone. College doesn’t pay for itself you know.” Dean chuckled and glanced at Sam, licking his lips as he thought about his next move. “You know, you kind of saved my life tonight.”

“No, I mean, I’m sure you could have taken that guy you’re not a small man.”

“No, but you still saved my ass. Thanks. My own superhero.” Sam laughed softly, and Dean was sure he had never heard a more musical sound. He had to say something before he chickened out all over again.

“Listen, Sam… would you… I mean-”

“Yeah.”

“Yeah?” Sam nodded, a big smile on his face, his dimples showing, and Dean knew he was so fucking screwed.

…


	4. First Date

**Summary for the Chapter:**

> Sam & Dean get to go on their first date

**Notes for the Chapter:**

> WOW. If ya'll follow me on tumblr (https://codependent-idiots.tumblr.com/) then ya'll know I've been trying to get this stuff updated. ANYWAYS. Yay new chapter!
> 
> P.S. - if you don't follow me on tumblr, you should check it out - I got some stuff posted over there that you might enjoy!

Sam let out an unhappy sound as he slid onto a stool at the bar. He had gone out with his friends tonight, promised weeks ago - Conner was playing with his band at a local dive bar, and he wasn't having any fun. Dean had fucking finally asked him out, and he had to turn him down for this. But he had invited Dean to come join them, so they could at least get to know each other a little more.

Dean said he'd try, but Sam has been here over an hour and no sign of the older man.

Like he'd wanna spend time with a bunch of college kids.

Fuck, Sam felt stupid. Like someone who looked like that would want someone like him.  
…

Dean stared at Sam from across the bar - like a fucking creeper, he noted - but he couldn't bring himself to go over there and talk to him. Fuck, he'd love nothing more than to go over there, buy him a drink, and take him onto the dance floor and move with him wrapped around him.

Dean was a fucking pansy and he hated himself for it.

Sam was right there.

Dean took a sip from his drink and watched as a woman walked up to Sam and slipped an arm over his shoulders, holding him at her side as she talked to him. He tensed up a bit as he saw Sam lean into her -no he wasn't jealous why would he be jealous nope he wasn't jealous not at all.  
…

"Hey." Sam looked up at Celia, one of his friends who had come to see Conner play. She slipped a slim arm around his shoulders and gave him a hug. "Sorry he didn't show." Conner was a loudmouth, having told all their friends about Dean, so now they all teased him relentlessly. "But hey, buck up. This really good looking guy over there keeps looking at you."

Sam looked in the direction she was tilting her head to see a guy in a suit looking over at him. Yeah, sure, he was attractive with his dark hair and his dark blue eyes, but Sam didn’t want blue eyes. He wanted green.

…

“Castiel, this is a bad idea and you know this.” Castiel just made a noncommittal noise as he fixed his tie. “Why don’t you leave the matchmaking to the Cupids?”

“This one is personal, as I’m sure you are aware,” is all he said, giving Marco one final grin before he was gone, nothing in his place but the small flutter of wings.  
…

Dean slammed back his shot of whiskey as he watched some asshat in a suit approach Sam. Why the fuck couldn’t he go over there and talk to the guy? Dean could pick up someone with just a look, so why couldn’t he go talk to the guy he had actually asked out on a date?

Dean hadn’t even cared when Sam said he had plans with his friends but that Dean could come along - if it meant he got to go out with Sam, he couldn’t care less. So he had come out, and he had seen Sam immediately - like he was hard to miss - and was all set to go over there and chat him up, when he found himself nervous.

Dean didn’t do nervous. He didn’t do feelings typically - he had more of a love em and leave em mentality - and when he had realized that he was way too hyped up to go over there and see Sam, it made him pause.

Sam was this gorgeous, smart, amazing guy, and Dean was just … Dean. He could fix up cars, could repair broken pieces of technology, and had a decent job, but he wasn’t anything special.

The whiskey had warmed him up a bit, and he squared his shoulders, ready to go finally talk to Sam, instead of watching him from a distance like some creepy stalker. Dean saw the bitch in the suit get them some drinks, but Sam didn’t look interested, so Dean thought that maybe he still had a chance.  
…

“Can I buy you a drink?” the guy asked Sam, who just shrugged. The guy tapped his finger on the bar top, and there were two drinks in front of them almost instantly. “You look like you could use one,” he said softly, smiling again. Sam chuckled but pushed the drink away.

“Thanks, but I’m waiting for someone.” Sam looked away, but the guy was persistent it seemed.

“Me too. My name is Jimmy.” Sam glanced at him, using the long-practiced tactic of hiding behind his bangs when someone talked to him to survey the guy. He was tall, maybe a little under 6 feet, with dark hair - Sam could see the beginnings of gray starting to streak through the dark tresses though - and his dark blue eyes crinkled up in the corners as he smiled at Sam; his voice was deep, more gravely than Sam would have imagined, but also just… there; he had one tone for everything it seemed.

Sam wasn’t overly impressed, but he was still polite, and hadn’t tried to get into Sam’s pants yet, so he had to give him kudos for that.

“Sam.” The man smiled, and Sam had a brief flash of familiarity as the guy glanced up and away from him.

“Hey.” Sam turned and grinned, seeing the way Dean eyed up the guy in the suit, who now looked pleased with himself as he got up and walked away. Dean met Sam’s eyes and grinned now too. “Sorry I’m late.”

“I’m just glad you’re here.” Conner’s band began to play right then, and Dean bit his lip as he glanced at Sam.

“You wanna dance?” Sam nodded and let the older man pull him out into the crowd.  
…

“Guess it does not matter which form they are in, Dean will always be easy to rile up,” Marco said as Castiel returned, who looked smug. “What happened to not interfering?”

“I’m not. I just wanted a drink,” he said simply, sitting back in his seat and watching the scene unfold.  
…

Sam and Dean found themselves tucked into a back booth, talking quietly to each other as the music played around them.

“So you’re fixing up a car from pretty much nothing?” Sam asked, intrigued. Dean chuckled and nodded.

“Yeah, it came in as a heap of junk ready to be scrapped. Lenny, my boss, was gonna just trash it once we scrounged it for parts, but I was able to talk him into letting me keep this one as a project. Had to take a bit out of my paycheck to pay for it, but I think I can get it up and running.”

“And what kind of car is it?” Sam asked, and Dean felt himself flush under the admiration in Sam’s eyes.

“I had to look it up, but it looks like an Impala. And older style, not sure of the year yet. Won’t know till I can get a little more of it back into shape.” Sam nodded, clearly impressed. “Enough about me,” Dean said, wanting to change the subject. “You’re in college? For law?” Sam flushed now and nodded.

“Yeah, just in my pre-req classes right now.” Dean gave him a blank look and Sam chuckled. “The classes required before I can start the law classes.”

“Oh. Cool. That’s impressive. I mean, really impressive.”

“And building cars from the bottom up isn’t?” Sam asked, easily telling where Dean was going with the conversation. “You’re fucking amazing. You ever thought about college? Imagine what you could do with an engineering degree or something.” Dean shrugged, taking a sip of his beer. He had never been one for school - it wasn’t that he wasn’t smart, he was smart as fuck, but he just didn’t have the patience for it. Sam could tell this was a sore subject and easily dropped it. “I’m glad you came out tonight.”

Dean met his eyes and licked his lips as he sat his glass down.

“I’m glad you said yes when I asked you out.” Sam had to look away now, cheeks turning a steady pink.

Dean was sure he hadn’t seen anyone more attractive in his life.

The two of them were just staring at each other for a moment, when Sam’s friend Celia came up.

“Sam, we’re all getting ready to go! Do you need a ride or….?” she trailed off, looking between the two of them - Dean had an arm slung around the back of the booth, and Sam had unconsciously been leaning into his side. Sam glanced at Dean, who gave Celia his best smirk. Sam could literally see her falling for his charm.

“I’ll make sure he gets home okay.”

“Oh… okay. Bye,” she said dazedly, hurrying away from them. Sam laughed and turned to Dean.

“Does that look work on everyone?” Dean shrugged and took a sip of his beer, looking very proud of himself.  
…

As the night got later, Sam found himself being walked home by Dean, who had slipped an arm around his waist. Sam was enjoying this way too much, but he worried. Was Dean expecting him to sleep with him? Sam wasn’t against one-night stands, sometimes people just needed that release, but he didn’t want that with Dean.

He found something inside of him was just saying that Dean was the one. Sam didn’t believe in soulmates, not at all, but something about Dean just made him doubt anything he ever knew.

Dean liked having Sam so close. When he had his arm around him, it was like everything that he had ever wanted had just fallen into place. Sure, he was beyond sexually attracted to Sam, no doubts about that, but it was more than that. It was like Sam was meant to be by his side, and Dean by his.

When they reached Sam’s apartment building, Dean let his arm slip from Sam’s waist, almost reluctantly.

“This was fun,” Sam said, tilting his head down a bit, making himself seem so much smaller than Dean, even when he stood three inches taller than him. Dean grinned and stepped a bit closer.

“This was a lot of fun.” Sam bit his lip as Dean got closer, and found himself pulling away a bit. Dean smirked but took a step back. “I’d like to do this again Sammy.” Sam nodded, Dean reminded of a puppy with the enthusiasm the younger man showed.

“I don’t work tomorrow. I can come by the garage when you get off?” Dean nodded and reached for Sam’s hand, grabbing it and pressing a quick kiss across his knuckles.

“Sounds good Sammy. I”ll show you the car I’m working on. Goodnight.”

“Night,” Sam said, breathless as he stumbled up the steps and into the building. Dean made sure he was inside before he began the walk back to his own apartment.


	5. Second Date, First Kiss

**Summary for the Chapter:**

> Sam & Dean grow a little closer.

**Notes for the Chapter:**

> HOLY SHIT. I didn't think I'd ever get this updated. Hell, I don't know if anyone is even gonna read this? But screw it, here it is!

Sam was trying to brush his hair, hearing Conner cat-calling from the living room.

“Oh yeah Sam, work it. Work that hairbrush baby!” Sam took two steps out of the small bathroom and tossed the brush at his roommate, who just laughed as he held up his hands in defense. 

“You’re an ass,” Sam grumbled as he grabbed his jacket.

“But you love me anyway. Now show me some skin baby, let me see you work it!” Conner was still laughing as Sam scowled at him. “Oh come on man, you’ve been pretty much  _ celibate _ since we started rooming together. Like I’m not gonna give you shit now that you’re on your way to get laid.”

“I’m not-” Sam started, groaning as he glared at his friend. “He’s just gonna show me the car he’s been building. That’s all.”

“Think it’s got a big backseat?” Conner asked, wiggling his eyebrows. Sam groaned and grabbed his keys, stomping out of the apartment, his friend’s teasing ringing in his ears.

…

Max was headbanging as Dean tuned the radio in the half-car he was working on. 

“Don’t you have your own job to do?” Dean muttered to his coworker, who stopped headbanging to give him a large grin.

“Nah man, they just pay me to look pretty.” Dean snorted a laugh as he disconnected some wires to just reconnect them. “I’m ‘spose to do an oil change on this ol’ lady’s car, but she ain’t here yet, so I’m gonna just annoy you until your boytoy comes by.” Dean glared at him now, but Max just gave him that carefree smile of his. “Oh I’m just fucking with you…. You think he could hook me up with that hot waitress with the legs?”

“Gotta be more specific cuz I’m pretty sure almost all waitresses have legs.”

“Ha ha ha,” Max grumbled as he stood up and pulled his long hair back into a ponytail. “Such a class act Dean.” Dean rolled his eyes as Max loped away to do his own job. Dean just wanted to focus on what he was working on today, and try not to think about how his shift ended in 10 minutes, and then Sam would hopefully come by, and Dean would see him again.

Dean couldn’t explain the pull he felt for the college student, but it was something he had never felt, or experienced, before. He had always heard crap about two people meeting, and like a peice of themselves had been found, blah-blah-blah, and Dean had always thought it was crap.

Now, he wasn’t so sure. It was like… it was like Sam was a part of himself he didn’t know he needed, but now that he had it, he didn’t want to let go.

He wondered if it was healthy to be this attached to someone so quickly, but the thought was gone as he saw Sam enter the garage and catch his eyes, giving him a large dimpled smile.

…

Sam didn’t know what it was, but seeing Dean in his work coveralls - which he had seen many times when he came into the diner - and covered in grime and in his environment, just made Sam’s heart pound loudly in his chest.

He almost felt like he had seen this before - Dean leaning over a shiny black car, fixing various things as music blasted over the speakers. He didn’t know where that thought or image had come from, but it just felt  _ right _ . Like this is something Dean should always be doing. 

“Hey,” Dean called, pulling Sam out of his daydream as he walked towards him. “You wanna come see the car?” Dean asked, trying not to get caught up in Sam’s eyes, which seemed especially bright today. 

“Sure. Lead the way.”

…

The car really put the term ‘half-finished’ to good use - Dean had straightened out what he could of the frame, had polished and repainted the parts of the black metal that he could, and had the radio working. He had knocked the dents out of the sides, the trunk, and the roof, and although he had to physically pry it open, he had gotten the trunk usable. 

“It’s not much, but she’s my baby. I’m gonna get her looking good and up and running before you know it. Did find a half-crushed box of cassette tapes in the front floorboard,” Dean said, tilting his head to the dented box on a nearby workstation. “And this.” Dean said, going to the workstation and grabbing what appeared to be some part of the dash. Sam looked over his shoulder and was surprised by the chill that ran down his spine.

It was a broken and bent piece of the dash, chipped and torn. But there, right in the middle, practically pristine, was a carving.

_ ‘D.W.’ _ and ‘ _ S.W.’ _

“Must have been who this beauty belonged to before,” Dean said, sitting it down. “Heh, if my last name was different, it could almost be us,” he said quietly, glancing at Sam, who was blushing now. “Think I’ll put it back in the car when I get it fixed up. Figure it’s just as important as the rest of it, ya know?”

Sam nodded, staring at the carvings again before he glanced back at the car.

“It’s a 67 Impala,” he said, the type and style of car just jumping into his mind - how he knew this, he had no idea; he didn’t know jackshit about cars. Dean raised an eyebrow at him, making Sam blush again from just the look. 

“You think so?”

“Yeah… yeah. I do.”

…

Dean had finished what he was doing and covered up the car before he and Sam decided to walk to his apartment so he could shower and change before they went to get something to eat. Sam had said he hadn’t cared, but Dean was adamant about not smelling like a hot oily mess, so Sam had relented.

Dean didn’t live too far from the garage, in a small one bedroom apartment. Sam stood in the living room, looking at the few posters and knick knacks that covered the walls as he heard the shower start. He tried not to imagine Dean, naked, the warm water of the shower running over his shoulders and chest and down to his-

Sam had to seriously pull himself together. 

Dean was no better off - he had a growing problem while he was in the shower, just  _ knowing _ that Sam was in the other room, could walk in, could join him…

Dean groaned and thumped his head against the wall. He needed to think of something else to make this problem stop before it got out of hand, so to speak. Thinking of his boss, the greasy grumbling old man that he was, did the trick. 

Dean had to get his head together before he made himself look like an idiot in front of Sam.

…

  
  


When Dean came out of the bathroom, dressed in jeans and a black shirt, his face slightly flushed, Sam had to look away. As hot as he thought Dean was in his work coveralls, it was  _ nothing _ compared to the way he looked in jeans and a t-shirt. Really, there was nothing this man  _ couldn’t  _ pull off. 

“So, what do you want to do?” Dean asked, letting his eyes trail over Sam, licking his lips as he watched him.

“Uh…Maybe… maybe we should go get something to eat?” HIs voice fucking cracked - great, that’s attractive. He could see Dean eyeing him, and his whole face flushed, even up to the tips of his ears. 

“Sounds good. Come on Sam, let’s go get some dinner.”

…

After dinner, they were heading back to Sam’s apartment. Sam’s phone started ringing about a block away, and he rolled his eyes when he realized it was his roommate.

“ _ So, did ya get laid yet?” _

“I’m coming home right now,” he said, choosing to ignore him.

“ _ Is your mechanic friend walking you home like a gentleman?”  _ Sam glanced at Dean to see him looking at him curiously.

“Yes…”

“ _ Awesome! I’m out for the night. Have fun big boy.” _ He hung up on Sam, and Sam could only imagine how red his face was right now. Dean must have heard that last part, because he had a light dusting of pink spreading over his freckled cheeks. As they continued to walk, he could see Dean staring at him every few minutes. Sam was sure his cheeks were permanently red now as they got to his apartment building. 

He was almost tempted to ask Dean to come up with him - hell, there was nothing wrong with that, right? Dean could see how uncomfortable Sam was though, and just held onto his hand.

“This was fun Sammy,” he said, tugging the taller man a little closer to him. Sam came easily, face still red. Dean thought it was adorable. He pressed a little closer and Sam automatically leaned down so they could meet in a kiss. Sam made a small noise in the back of his throat as Dean pulled away. “Night Sammy.”

“Night,” he said softly as Dean gave him one more kiss. He needed to get out of here before he just took Sam to his apartment anyway. He made sure to step away and watch Sam go into his apartment before he headed home, the feeling of Sam’s lips still on his.

**Author's Note:**

> Thanks for reading! <3  
> I hope ya'll liked it!


End file.
